Citation: ZHANG Chenglu, WANG Huayu, LI Yilin, WANG Yiming, GONG Rongqing, SUN Yuedong, SONG Fulu. Synthesis of 4-Phenyl-1, 3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B[J]. Chinese Journal of Applied Chemistry, ;2019, 36(7): 749-757. doi: 10.11944/j.issn.1000-0518.2019.07.180381 shu

Synthesis of 4-Phenyl-1, 3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: ZHANG Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 29 November 2018
Revised Date: 4 January 2019
Accepted Date: 25 February 2019

Fund Project: Supported by the Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)the Technology Research Program of Liaoning Provincial Department of Education 2009A426

Figures(3)

Protein tyrosine phosphatase-1B(PTP1B) is an important target for anti-diabetic treatment. That means the creation of PTP1B inhibitors with excellent activity is undoubtedly of great significance. In this paper, eleven molecules with novel structures(ZLXZ1-ZLXZ11) containing 1, 3-selenazole and 1, 2, 4-triazole active blocks were designed and synthesized. Their structures were characterized by Fourier transform infrared spectrometer(FTIR), nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometry(HRMS). First, ZLXZ1 and ZLXZ11 were selected for molecular docking simulation with PTP1B on MOE 2015.10. As a result, π-H action and hydrogen bonding are formed respectively between the selenium atom on the selenazole ring in ZLXZ1 and the secondary catalytic sites Tyr46 and Asp48 in PTP1B. The selenium atom on the selenazole in the ZLXZ11 molecule forms a hydrogen bond with Asp 181, which facilitates the binding of the molecule to PTP1B. On this basis, the inhibitory activities of 11 target molecules were evaluated. The results show that the inhibition rates of the target molecules are all above 87.02%, in which three target molecules are better than that of the positive control, oleanolic acid, which indicates that these novel structures are expected to be potential PTP1B inhibitors.
- 1, 3-selenazole,
- 1, 2, 4-triazole Schiff base,
- molecular docking simulation,
- protein tyrosine phosphatase-1B inhibitor
1. [1]
  Cooke D W, Plotnick L. Type 1 Diabetes Mellitus in Pediatrics[J]. Pediatr Rev, 2008,29(11):374-385. doi: 10.1542/pir.29-11-374
2. [2]
  Yip S C, Saha S, Chernoff J. PTP1B:A Double Agent in Metabolism and Oncogenesis[J]. Trends Biochem Sci, 2010,35(8):442-449. doi: 10.1016/j.tibs.2010.03.004
3. [3]
  Chen Y T, Tang C L, Ma W P. Design, Synthesis, and Biological Evaluation of Novel 2-Ethyl-5-Phenylthiazole-4-carboxamide Derivatives as Protein Tyrosine Phosphatase-1B Inhibitors with Improved Cellular Efficacy[J]. Eur J Med Chem, 2013,69:399-412. doi: 10.1016/j.ejmech.2013.09.017
4. [4]
  Omar K, Geronikaki A, Zoumpoulakis P. Novel 4-Thiazolidinone Derivatives as Potential Antifungal and Antibacterial Drugs[J]. Bioorg Med Chem, 2010,18(1):426-432. doi: 10.1016/j.bmc.2009.10.041
5. [5]
  Kline T, Felise H B, Barry K C. Substituted 2-Imino-5-Arylidenethiazolidin-4-one Inhibitors of Bacterial Type Ⅲ Secretion[J]. J Med Chem, 2008,51(22):7065-7074. doi: 10.1021/jm8004515
6. [6]
  Suresh K G V, Rajendraprasad Y, Mallikarjuna B P. Synthesis of Some Novel 2-Substituted-5-(Isopropylthiazole) Clubbed 1, 2, 4-Triazole and 1, 3, 4-oxadiazoles as Potential Antimicrobial and Antitubercular Agents[J]. Eur J Med Chem, 2010,45(5):2063-2074. doi: 10.1016/j.ejmech.2010.01.045
7. [7]
  Alsaid M S, Bashandy M S, Alqasoumi S I. Anti-breast Cancer Activity of Some Novel 1, 2-Dihydropyridine, Thiophene and Thiazole Derivatives[J]. Cheminform, 2011,42(22):137-141.
8. [8]
  Chandrappa S, Chandru H, Sharada A C. Synthesis and in Vivo Anticancer and Antiangiogenic Effects of Novel-Thioxothiazolidin-4-one Derivatives Against Transplantable Mouse Tumor[J]. Med Chem Res, 2010,19(3):236-249. doi: 10.1007/s00044-009-9187-7
9. [9]
  Garuti L, Roberti M, Pession A. Synthesis and Antiproliferative Activity of Some Thiazolylbenzimidazole-4, 7-diones[J]. Bioorg Med Chem Lett, 2001,11(24):3147-3149. doi: 10.1016/S0960-894X(01)00639-4
10. [10]
  Martin J R, Roger R J, Ernest A H, et al. 1-Dimethylcarbamoyl-3-Substituted-5-Substituted-1H-1, 2, 4-Triazoles: US, US5015652[P]. 1991.
11. [11]
  Howatt K A. Carfentrazone-Ethyl Injury to Spring Wheat Is Minimized by Some ALS-Inhibiting Herbicides1[J]. Weed Technol, 2005,19(4):777-783. doi: 10.1614/WT-04-206.1
12. [12]
  Wang B L, Liu X H, Zhang X L. Synthesis, Structure and Biological Activity of Novel 1, 2, 4-Triazole Mannich Bases Containing a Substituted Benzylpiperazine Moiety[J]. Chem Biol Drug Des, 2011,78(1):42-49. doi: 10.1111/j.1747-0285.2011.01132.x
13. [13]
  Yang B, He Q J, Zhu D Y. Antiproliferative Activity of Contragestazol(DL111-IT) in Murine and Human Tumor Models in Vitro and in Vivo[J]. Cancer Chemother Pharmacol, 2006,57(2):268-273. doi: 10.1007/s00280-005-0049-9
14. [14]
  Xia Y, Fan Z, Yao J. Discovery of Bitriazolyl Compounds as Novel Antiviral Candidates for Combating the Tobacco Mosaic Virus[J]. Cheminform, 2006,37(33):2693-2698.
15. [15]
  Xu F, Wen J, Yong B. Design and Synthesis of Novel Antifungal Triazole Derivatives with Good Activity and Water Solubility[J]. Chinese Chem Lett, 2013,24(4):303-306. doi: 10.1016/j.cclet.2013.01.047
16. [16]
  Aiken S P, Brown W M. Treatment of Epilepsy:Existing Therapies and Future Developments[J]. Front Biosci A J Virt Libr, 2000,5(1)E124. doi: 10.2741/aiken
17. [17]
  Polucci P, Magnaghi P, Angiolini M. Alkylsulfanyl-1, 2, 4-Triazoles, A New Class of Allosteric Valosine Containing Protein Inhibitors Synthesis and Structure Activity Relationships[J]. Eur J Med Chem, 2013,56(2):437-450. doi: 10.1021/jm3013213
18. [18]
  Reddy T R K, Chan L, Guo X. Design, Synthesis and SAR Exploration of Tri-substituted 1, 2, 4-Triazoles as Inhibitors of the Annexin A2 S100A10 Protein Interaction[J]. Bioorg Med Chem, 2014,22(19):5378-5391. doi: 10.1016/j.bmc.2014.07.043
19. [19]
  Bekircan O, Bektas H. Synthesis of New Bis-1, 2, 4-Triazole Derivatives[J]. Molecules, 2006,11(6):469-477. doi: 10.3390/11060469
20. [20]
  Brandt C D, Kitchen J A, Beckmann U. Synthesis and Structures of 3, 5-Disubstituted 1, 2, 4-Triazole Head Units and Incorporation of 3, 5-Dibenzoyl-1, 2, 4-Triazolate into New[J]. Supramol Chem, 2007,19(1):17-27.
21. [21]
  Lakshman B A, Gupta R L, Prasad D. Quantitative Structure Activity Relationships for the Nematicidal Activity of 4-Amino-5-Substituted Aryl-3-mercapto-(4H)-1, 2, 4-triazoles[J]. Indian J Chem, 2010,49(12):1657-1661.
22. [22]
  ZHANG Chenglu, XI Huan, SHA Yuting. Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives[J]. Chinese J Appl Chem, 2017,34(3):308-315.
23. [23]
  Panda S, Nayak S. Antibacterial, Antioxidant and Anthelmintic Studies of Inclusion Complexes of Some 4-Arylidenamino-5-Phenyl-4H-1, 2, 4-Triazole-3-Thiols[J]. Supramol Chem, 2015,27(10):679-689. doi: 10.1080/10610278.2015.1075533
24. [24]
  LIU Bo, XU Caiding, ZHOU Xunjun. A Novel Synthesis of Selenourea and 2-Amino-selenazoles[J]. Chem Reagents, 1993,15(6):334-335.
25. [25]
  Rakse M, Karthikeyan C, Deora G S. Design, Synthesis and Molecular Modelling Studies of Novel 3-Acetamido-4-Methyl Benzoic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase-1B[J]. Eur J Med Chem, 2013,70(12):469-476.
26. [26]
  ZHANG Chenglu, CHENG Anqi, TANG Jie. Synthesis and Biological of the Novel Mannich Bases of 5-Alkyl-1, 2, 4-triazole[J]. Chinese J Appl Chem, 2016,33(5):554-564.
27. [27]
  PANG Xiaobin, XIE Xinmei, WANG Shoubao. High-throughput Screening of Human Protein Tyrosine Phosphatase PTP1B Inhibitor[J]. Acta Pharm Sin, 2011,46(9):1058-1064.
1. [1]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
2. [2]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
3. [3]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
4. [4]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
5. [5]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
6. [6]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
7. [7]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
8. [8]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
9. [9]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
10. [10]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
11. [11]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
12. [12]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
13. [13]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
14. [14]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
15. [15]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
16. [16]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
17. [17]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
18. [18]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
19. [19]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
20. [20]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(418)
HTML views(50)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142